Patent GB-815925-A (GB)
Title: New biguanide salts
Inventor: SENIOR NORMAN
IPC: C07C279/26
Filed: 1956-06-06
Abstract: Aqueous detergent compositions comprise (a) salts of polyhydroxy aliphatic carboxylic acids containing not more than 6 carbon atoms with bis-biguanides of the formula <FORM:0815925/III/1> (wherein A is phenyl, halophenyl or alkylphenyl, the alkyl groups containing at most 3 carbon atoms, X is a direct link or an alkylene radical of at most 3 carbon atoms, m is an integer from 2 to 12 and the polymethylene chain, (CH2)m, may be interrupted by oxygen atoms), and (b) surface active quaternary ammonium salts such as cetrimide (i.e. hexadecyltrimethylammonium bromide containing smaller amounts of related alkyltrimethylammonium salts such as dodecyl- and tetradecyl-trimethylammonium chlorides and bromides).  An aqueous solution of 1 : 6 - di - (N1 - p - chlorophenyldiguanido-N5)-hexane digluconate containing cetrimide and a composition containing, in addition to these ingredients, cetostearyl alcohol, liquid paraffin and arachis oil are described.  Specifications 705,838 and 785,937, [both in Group IV (b)], are referred to.ALSO:The invention comprises salts of polyhydroxy aliphatic carboxylic acids containing not more than 6 carbon atoms with bis-biguanides of the formula <FORM:0815925/IV (b)/1> (wherein A is phenyl, halophenyl or alkylphenyl, the alkyl groups containing at most 3 carbon atoms, X is a direct link or an alkylene radical of at most 3 carbon atoms, m is an integer from 2 to 12 and the polymethylene chain, (CH2)m, may be interrupted by oxygen atoms) and their preparation by interaction of the acid or a salt thereof with the bis-biguanide or a salt thereof, advantageously in a liquid medium such as water.  The acid is preferably used in the form of a lactone, or, alternatively, an alkaline earth metal salt of the acid is interacted with a salt of the bis-biguanide with an acid, the alkaline earth metal salt of which acid is insoluble in water. Examples describe the preparation of the di-D-gluconates of 1 : 6-di-(N1-p-chlorophenyldiguanido - N5) - hexane, 1 : 6 - di - N1-p - tolyldiguanido - N5) - hexane, 1 : 2 - di - (N1-p - chlorophenyldiguanido - N5) - ethane, 1 : 4 - di - (N1 - p - chlorophenyldiguanido - N5) - butane, 1 : 10 - di - (N1 - p - chlorophenyldiguanido-N5) - decane, 1 : 6 - di - (N1 - p - chlorobenzyldiguanido - N5) - hexane, o  : o 1 - (N1 - p - chlorophenyldiguanido - N5) - di - n - propyl ether and 1 : 6 - di - (N1 - b  - phenylethyldiguanido - N5) - hexane from the appropriate bis-biguanide and D-glucono-delta-lactone in water.  In the Provisional Specification the bis-biguanides are represented by the general formula <FORM:0815925/IV (b)/2> wherein A is phenyl, alkylphenyl, alkoxyphenyl, nitrophenyl or halophenyl, R and R1 are hydrogen, alkyl or aralkyl, X and X1 are each a direct linkage or an alkylene radical of 1-3 carbon atoms, m is 2-12 and (CH2)m may optionally be interrupted, e.g. by oxygen atoms and/or aromatic nuclei. Specifications 705,838 and 785,937 are referred to.ALSO:Antibacterial compositions comprise one or more salts of polyhydroxy aliphatic carboxylic acids containing not more than 6 carbon atoms with bis-biguanides of the formula <FORM:0815925/VI/1> (wherein A is phenyl, halophenyl or alkylphenyl, the alkyl groups containing at most 3 carbon atoms, X is a direct link or an alkylene radical of at most 3 carbon atoms, n is an integer from 2 to 12 and the polymethylene chain (CH2)m may be interrupted by oxygen atoms) in admixture with a diluent or carrier.  Preferred compositions include aqueous solutions optionally containing excipients such as wetting or surface-active agents, e.g. condensation products of alkyl phenols with ethylene oxide and quaternary ammonium salts; and oil-in-water emulsions, e.g. aqueous gels or creams, ointments or pastes, the aqueous gels optionally containing water-miscible agents such as glycerol and/or gelling or thickening agents such as ethylcellulose and the oil-in-water emulsions or cream preparations in general optionally containing non-toxic hydrocarbon products, e.g. liquid paraffin, white or yellow soft paraffin and fatty alcohols, and/or non-toxic animal or vegetable fats or oils.  Examples describe the following compositions: aqueous solutions of, separately, (1 : 6-di-(N1 - p - chlorophenyldiguanido - N5) - hexane di - D - gluconate, 1 : 6 - di - (N1 - p - chlorobenzyldiguanido - N5) - hexane di - D - gluconate, o  : o  - (N1 - p - chlorophenyldiguanido-N5) - di - r - propyl ether di - D - gluconate and 1 : 6 - di - (N1 - b  - phenylethyl - diguanido-N5)-hexane di-D-gluconate; and compositions containing in addition to the first-named active ingredient and water the following materials: (1) a condensation product obtained from octyl cresol and 8 to 10 molecular proportions of ethylene oxide; (2) cetrimide; (3) liquid paraffin, cetostearyl alcohol and cetomacragol; (4) ethylcellulose and glycerol; (5) cetrimide, cetostearyl alcohol, liquid paraffin and arachis oil; and (6) lanoline and yellow soft paraffin.  In the Provisional Specification the bis-biguanide salts are defined in somewhat wider terms.  Specifications 705,838 and 785,937, [both in Group IV (b)], are referred to.